Triethylamine → HCID 10088201, compound

HRID 1077823Notes

Reaction equation

HRID 1077823 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][CH2:18][N:17]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10467846HCID 10467846, compound

Product 1

HCID 10088201HCID 10088201, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

460 mg of 3-(3-cyclopentyloxy-4-methoxyphenyl) pyrrolidine and 214 mg of triethylamine were dissoved in 15 ml of dichloromethane and cooled in an ice bath. During agitation, 229 mg of ethyl chloroformate was added in drops. After dropping, agitation was continued for 1 hour at a room temperature. Thereafter, the agitated solution was poured into ice water and then extracted with dichloromethane. After organic layers were cleaned by water and dried over magnesium sulfate, it was concentrated under a reduced pressure. The residue was purified by means of the silica gel column chromatography to obtain 92 mg of Compound No. 4 in Table 1.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with dichloromethane
  3. dry with materialdried over magnesium sulfate, it
  4. concentrationwas concentrated under a reduced pressure
  5. customThe residue was purified by means of the silica gel column chromatography

Sources & evidence

ORD record
ord-ba844bd7ec6442f4a93f73b67d8c3511
Source dataset
uspto-grants-1996_08
Patent number
US05545647

Reaction notes

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